Hydrochloric Acid → HCID 22170609, compound

HRID 491534Notes

Reaction equation

HRID 491534 reaction equation
[Cl:1][CH2:2][CH2:3][O:4][C:5]1[CH:6]=[C:7]([CH2:11][C:12]([O:14]C)=[O:13])[CH:8]=[CH:9][CH:10]=1.[OH-].[Na+].Cl>CO>[Cl:1][CH2:2][CH2:3][O:4][C:5]1[CH:6]=[C:7]([CH2:11][C:12]([OH:14])=[O:13])[CH:8]=[CH:9][CH:10]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 22170578HCID 22170578, compound

Product 1

HCID 22170609HCID 22170609, compoundYield 99%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Methyl 3-(2-chloro-ethoxy)-phenylacetate (7.0 g, 32.9 mmol) was dissolved in methanol (40 mL) and 6N NaOH (5.5 mL) was added. The mixture was stirred at room temperature overnight then acidified by addition of 6N hydrochloric acid (5.5 mL). A white precipitate formed which was filtered, washed with 1N HCl, water and dried to afford 3-(2-chloroethoxy)-phenylacetic acid (6.5 g, 99%). 1H NMR (CDCl3) δ3.55 (s, 2H), 3.75 (t, 2H), 4.15 (t, 2H), 6.78 (dd, 1H), 6.80 (d, 1H), 6.84 (dd, 1H), 7.16 (dd, 1H).

Workup

  1. customA white precipitate formed which
  2. filtrationwas filtered
  3. washwashed with 1N HCl, water
  4. customdried

Sources & evidence

ORD record
ord-26e5de5a7c5744e89dd0012acdc8618a
Source dataset
uspto-grants-2009_05
Patent number
US07531556B2

Reaction notes

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